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Go There: A Weekender’s Guide to Portland, Oregon

Spending a weekend in PDX? Here's how to shop, eat and explore like a local in Portland, Oregon. 

By Dmytryk Carreño on April 21, 2023

People dine on a restaurant patio in downtown Portland Oregon USA in the evening.

Portland, Oregon, has seen a lot of change in the past few years, thanks to a steady influx of new residents and tourists who desire to explore the ‘Weird City.’ 

But even though PDX might look a little different than it did even three years ago, one thing has proven certain since 2020: You can’t kill weird.

The city is a great place for delicious food, stellar live music, mind-bending art and stunning natural beauty. Every corner of town has its own unique personality and one-of-a-kind treasures. We’re here to let you in on ‘em.

So without further ado, here’s the weekender’s guide to Portland.

Where To Stay in Portland, OR

There’s no shortage of local rentals or hotels. But you’re not here for typical recs. You’re here for a good time, not a long time. You want an experience. Hotel Lucia and The Royal Sonesta hotels are sweet spots to put up your feet if you want to stay downtown and close to the usual retail shops. Staying in either of these two hotels also gets you close to Powell’s City of Books, a must-visit bookshop that takes up a whole city block and is filled to the gills with hundreds and hundreds of books. You’re also a stone’s throw from the Pearl District, home to many of the more Portland-specific shopping and eating experiences. But if you want to stay outside downtown, check out the Kennedy School.

At McMenamins Kennedy School, you get a little bit of everything. Restaurants, bars, lounges and lodging, all in the unmistakable McMenamins style. McMenamins is a family-owned chain with over sixty locations across Oregon and Washington, with three overnight-stay locations and 12 restaurants/bars in Portland alone! In other words, you’re sure to find a McMenamins hang in whatever part of town you wind up in.

What To Do in Portland, OR

If you’re coming to Portland, you must visit the parks. You’ll always find people in the parks, regardless of the month or weather, and for a good reason. The parks are just gorgeous. And in the warmer months, there are various park events to attend. Mt. Tabor is crisscrossed with walking trails, playgrounds and sitting areas to look out across the city, perfect for an afternoon outing with your partner, your dog or just for some alone time. 

Bring your comfy shoes. Laurelhurst Park has a big pond where ducks and geese are found communing with leashed dogs and elderly bird watchers. This is the perfect park to stretch out with a cup of coffee and a good book. Then there are the Japanese Gardens right next to the Portland Zoo. Visit one and the other in the afternoon, then hit up Northwest 23rd Street for some good eats.

Where To Eat & Drink in Portland, OR

You can’t come to Portland and not visit the food carts. And, if you do, you’ve sort of missed the point. Food carts are the city’s beating heart, making it so special. This isn’t like NYC hot dog stands or L.A.’s traveling taco trucks. This is something entirely different. These are food cart pods. These are collectives, little cities in and of themselves where you can find every kind of food you can imagine… if you know which pod to visit. Some local favorites include Titos Taquitos, Yoshi’s Sushi, Bing Mi and Farmer and The Beast.

There are pods in just about every single neighborhood of Portland, and if there isn’t a cart that serves your favorite drink, there’s always a bar nearby (Portland is home to one of the highest bar-to-household ratios in the continental U.S.). So it shouldn’t come as a surprise that Portland is one of the best foodie cities in the country; from Asian fusion to classic BBQ and desserts from every corner of the world, you’re bound to find something to satisfy whatever you’re craving. 

Where To Shop in Portland, OR

Portland is not big on malls. There are a couple of traditional malls in the city, but they remain primarily empty compared to other cities’ shops, even around the holiday season. If you are looking for more of the usual chains, some places are in Portland’s Pearl District — Madewell, Anthropologie, Filson, Patagonia, etc. But to get to the heart of the city, you’ll need to experience one of the locally-owned or independent stores.

If you want something a little more unique, you’ll have to get outside of downtown altogether. Along Northwest 23rd St., you’ll find a shop called Paxton Gate, a surreal and macabre collection of beautiful and bizarre artwork, taxidermy and collectibles. Paxton Gate is helping keep Portland weird. Up on Southeast Hawthorne Blvd., you’ll find the massive House of Vintage, a warehouse filled with styles for every sensibility. Into streetwear? Try The Darkside Initiative on Burnside or INDEX off of Couch St. Oh, and there are two Powell’s Books for all the voracious readers — the big one downtown and a smaller one on Southeast Hawthorne!

Live Music in Portland, OR: A Local Obsession

Portlanders love their beer and their coffee and their food carts, and their local mom-and-pop shop. But if there is one thing they are especially serious about, it is live music, specifically in the summer.

Summer in the Weird City is wild! There’s something happening every single day, from fairs on every major street to the city’s infamous Naked Bike Ride. The Cathedral Park Jazz Festival, the Waterfront Blues Festival, major bands playing at McMenamins Edgefield, indie rock bands rattling the walls at Wonder Ballroom, and so much more. Look up who’s playing where when you book your trip. Who knows, maybe you’re favorite band will be coming into town right when you are…

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